EP4063353A1 - Organische verbindung und organische elektrolumineszente vorrichtung mit verwendung davon - Google Patents

Organische verbindung und organische elektrolumineszente vorrichtung mit verwendung davon Download PDF

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Publication number
EP4063353A1
EP4063353A1 EP20890077.9A EP20890077A EP4063353A1 EP 4063353 A1 EP4063353 A1 EP 4063353A1 EP 20890077 A EP20890077 A EP 20890077A EP 4063353 A1 EP4063353 A1 EP 4063353A1
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Prior art keywords
group
compound
organic
electron transport
layer
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English (en)
French (fr)
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EP4063353A4 (de
Inventor
Woojae Park
Minsik EUM
Jaeyi Sim
Jeongkeun Park
Hyosuk SON
Yonghwan Lee
Songie HAN
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Solus Advanced Materials Co Ltd
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Solus Advanced Materials Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom

Definitions

  • the present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, to an organic compound having excellent heat resistance, carrier transport capability, luminescence capability, electron injection/transport capability, electrochemical stability, and the like; and an organic electroluminescent device which, by including the organic compound in one or more organic layers, has improved characteristics such as improved luminous efficiency, driving voltage, and lifespan.
  • organic electroluminescent devices In organic electroluminescent devices (hereinafter, "organic EL devices"), upon application of voltage between two electrodes, holes are injected from an anode (e.g., positive electrode) to an organic layer and electrons are injected from a cathode (e.g., negative electrode) to the organic layer. Injected holes and electrons meet each other to form excitons, and light emission occurs when the excitons fall to a ground state.
  • materials used for the organic layer may be classified into, for example, light-emitting materials, hole injection materials, hole transport materials, electron transport materials and electron injection materials according to their function.
  • Light-emitting materials may be classified into blue, green and red light-emitting materials according to their emission colors, and further into yellow and orange light-emitting materials for realizing better natural colors.
  • a host/dopant system may be employed in the light-emitting material to increase color purity and luminous efficiency through energy transition.
  • Dopant materials may be classified into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds which include heavy atoms such as Ir and Pt.
  • the developed phosphorescent materials may improve the luminous efficiency theoretically up to four times as compared to fluorescent materials, so studies are being conducted on phosphorescent dopants as well as phosphorescent host materials.
  • NPB, BCP and Alq 3 are widely known as materials used in the hole injection layer, the hole transport layer, the hole blocking layer and the electron transport layer, and anthracene derivatives have been reported as light-emitting materials.
  • metal complex compounds including Ir such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2 , which are known to have advantages in terms of efficiency improvement among light-emitting materials, are used as blue, green and red phosphorescent dopant materials, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.
  • the present invention is directed to an organic layer material of an organic electroluminescent device that is excellent in heat resistance, carrier transport ability, light-emitting ability, electrochemical stability, and the like, and specifically, to a novel organic compound applicable as an electron transport layer material.
  • the present invention is also directed to an organic electroluminescent device including the aforementioned novel organic compound, thereby having low driving voltage, high luminous efficiency, and improved lifespan.
  • the present invention provides an organic compound represented by the following Chemical Formula 1 or 2: (in Chemical Formulas 1 and 2,
  • the present invention provides an electroluminescent device comprising: an anode, a cathode, and one or more organic layer disposed between the anode and the cathode, wherein at least one of the one or more organic layer comprises the compound.
  • the compound of the present invention is excellent in terms of heat resistance, carrier transport capability, luminescence capability, electrochemical stability, and the like, and thus may be applicable as an organic layer material of an organic electroluminescent device.
  • an organic electroluminescent device having excellent light-emitting performance, low driving voltage, high efficiency and long lifespan characteristics as compared to conventional materials may be manufactured, and it is possible to manufacture a full color display panel with improved performance and lifespan.
  • the present invention provides a compound that may be used as a high-efficiency electron transport layer material having excellent heat resistance, carrier transport ability, light-emitting ability, electrochemical stability, and the like.
  • a pyrimidine moiety and a fluorene moiety or a benzofluorene moiety are bonded through a biphenylene group which is a linker to form a basic skeleton, and these are bonded to a meta-para position or a para-meta position and represented by Chemical Formula 1 or 2.
  • the compound of the present invention has a plate-like structure, while having asymmetry with respect to a major axis (e.g., long axis) of the molecule, and thus it is excellent in terms of heat resistance, carrier transport ability, light-emitting ability, electrochemical stability, and the like.
  • the organic EL device may have a low driving voltage, high luminous efficiency and current efficiency, and a long lifespan.
  • X 1 and X 2 are different from each other and are CR 3 or N, where one of X 1 and X 2 is N and the other is CR 3 . Accordingly, the compound of the present invention contains a pyrimidine moiety which is an electron withdrawing group (EWG) having high electron absorptivity.
  • EWG electron withdrawing group
  • R 3 is selected from: hydrogen, deuterium, halogen, a cyano group, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms.
  • X 1 may be CR 3
  • X 2 may be N
  • R 3 may be selected from: hydrogen, deuterium, halogen, a cyano group and a C 1 to C 40 alkyl group and may specifically be hydrogen or deuterium.
  • R 1 and R 2 may be the same as or different from each other, each independently being selected from: a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, a C 6 to C 60 arylphosphine group, a C 6 to C 60 arylphosphin oxide group, and a C 6 to C 60 ary
  • R 1 and R 2 may be different from each other and may each independently be selected from: a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. Specifically, R 1 and R 2 may be different from each other and may be a C 6 to C 60 aryl group.
  • R 1 and R 2 may be different from each other, and any one of R 1 and R 2 may be a biphenyl group or a terphenyl group, and the other may be a phenyl group.
  • Ar 1 is a substituent represented by any one of the following Chemical Formulas F1 to F6.
  • the substituents of the Chemical Formulas F1 to F6 are substituents which have electron donor group (EDG) characteristics with large electron donating properties, and by bonding with a pyrimidine moiety, which is an electron withdrawing group (EWG) having high electron absorptivity, through a biphenylene group which is a linker group, the entire molecule has a bipolar characteristic, and thus a bonding force between holes and electrons is high.
  • EWG electron donor group
  • Ar 1 may be a substituent represented by Chemical Formula F1.
  • the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the alkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group and the arylamine group of R 1 and R 2 , and the alkyl group, the aryl group, and the heteroaryl group of R 3 may each independently be substituted or unsubstituted with one or more substituents selected from: deuterium, halogen, a cyano group, a nitro group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a heterocyclo
  • the compound represented by Chemical Formula 1 or 2 according to the present invention may be embodied as a compound represented by Chemical Formula 3 or 4 below, but embodiments are not limited thereto.
  • the compound represented by Chemical Formula 1 or 2 according to the present invention described above may be embodied as the following Compounds 1 to 250.
  • the compound represented by Chemical Formula 1 or 2 according to the present invention is not limited by those exemplified below.
  • alkyl refers to a monovalent substituent derived from a linear or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples of such alkyl may include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl or the like.
  • alkenyl refers to a monovalent substituent derived from a linear or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms, having at least one carbon-carbon double bond. Examples of such alkenyl may include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl or the like.
  • alkynyl refers to a monovalent substituent derived from a linear or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms, having at least one carbon-carbon triple bond. Examples of such alkynyl may include, but are not limited to, ethynyl, 2-propynyl or the like.
  • cycloalkyl refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • examples of such cycloalkyl may include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine or the like.
  • heterocycloalkyl refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, where one or more carbons in the ring, preferably one to three carbons, are substituted with a heteroatom such as N, O, S or Se.
  • heterocycloalkyl may include, but are not limited to, morpholine, piperazine or the like.
  • aryl refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms which is in a structure with a single ring or two or more rings combined with each other.
  • a form in which two or more rings are pendant (e.g., simply attached) to or fused with each other may also be included.
  • Examples of such aryl may include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl or the like.
  • heteroaryl refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms.
  • one or more carbons in the ring preferably one to three carbons, are substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are pendant to or fused with each other may be included and a form fused with an aryl group may be included.
  • heteroaryl may include, but are not limited to, a 6-membered monocyclic ring including, for example, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl; a polycyclic ring including, for example, phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; 2-furanyl; N-imidazolyl; 2-isoxazolyl; 2-pyridinyl; 2-pyrimidinyl or the like.
  • alkyloxy refers to a monovalent substituent represented by R'O-, where R' refers to an alkyl having 1 to 40 carbon atoms, and such alkyloxy may include a linear, branched or cyclic structure. Examples of such alkyloxy may include, but are not limited to, methoxy, ethoxy, n-propoxy, 1 -propoxy, t-butoxy, n-butoxy, pentoxy or the like.
  • aryloxy refers to a monovalent substituent represented by RO-, where R refers to an aryl having 5 to 40 carbon atoms. Examples of such aryloxy may include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy or the like.
  • alkylsilyl refers to a silyl substituted with an alkyl having 1 to 40 carbon atoms and includes mono- as well as di- and tri-alkylsilyl.
  • arylsilyl refers to a silyl substituted with an aryl having 5 to 60 carbon atoms, and includes mono- as well as polyarylsilyl such as di- and tri-arylsilyl.
  • alkylboron group refers to a boron group substituted with an alkyl having 1 to 40 carbon atoms
  • arylboron group refers to a boron group substituted with an aryl having 6 to 60 carbon atoms.
  • alkylphosphinyl group refers to a phosphine group substituted with an alkyl having 1 to 40 carbon atoms, and includes mono- as well as di-alkylphosphinyl group.
  • arylphosphinyl group refers to a phosphine group substituted with a monoaryl or diaryl having 6 to 60 carbon atoms, and includes mono- as well as di-arylphosphinyl group.
  • arylamine refers to an amine substituted with an aryl having 6 to 40 carbon atoms, and includes mono- as well as di-arylamine.
  • fused ring refers to a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.
  • organic electroluminescent device including the compound represented by Chemical Formula 1 or 2.
  • the organic EL device includes an anode (e.g., a positive electrode), a cathode (e.g., a negative electrode), and one or more organic layers disposed between the anode and the cathode, and at least one of the one or more organic layers includes the compound represented by Chemical Formula 1 or 2.
  • the compound may be used solely or as a combination of two or more kinds thereof
  • the one or more organic layers may include one or more of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and at least one of the organic layers may include the compound represented by Chemical Formula 1 or 2.
  • the organic layer including the compound represented by Chemical Formula 1 or 2 may be selected from an electron transport layer and an electron transport auxiliary layer.
  • the one or more organic layer may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer
  • the electron transport layer includes the compound represented by Chemical Formula 1 or 2.
  • the compound represented by Chemical Formula 1 or 2 is included in the organic EL device as an electron transport layer material.
  • electrons may be easily injected from the cathode or the electron injection layer to the electron transport layer because of the compound of Chemical Formula 1 or 2, and may also rapidly move from the electron transport layer to the light-emitting layer, and thus holes and electrons in the light-emitting layer has a high bonding force.
  • the organic EL device of the present invention is excellent in luminous efficiency, power efficiency, luminance, and the like.
  • the compound of Chemical Formula 1 or 2 has excellent thermal stability and electrochemical stability, thereby improving the performance of the organic EL device.
  • Such a compound of Chemical Formula 1 or 2 may be used alone, or may be mixed with electron transport layer materials known in the art.
  • the electron transport layer material that may be mixed with the compound of Chemical Formula 1 or 2 may include an electron transport material commonly known in the art.
  • the applicable electron transport material may include an oxazole-based compound, an isoxazole-based compound, a triazole-based compound, an isothiazole-based compound, an oxadiazole-based compound, a thiadiazole-based compound, a perylene-based compound, an aluminum complex (e.g., Alq 3 , tris(8-quinolinolato)-aluminium), and a gallium complex (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)). These may be used alone or in combination of two or more.
  • a mixing ratio thereof is not particularly limited and may be appropriately adjusted within a range known in the art.
  • the one or more organic layers may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer
  • the electron transport auxiliary layer may include the compound represented by Chemical Formula 1 or 2.
  • the compound represented by Chemical Formula 1 or 2 is included in the organic EL device as an electron transport auxiliary layer material.
  • the compound of Chemical Formula 1 or 2 has a high triplet energy. For this reason, when the compound of Chemical Formula 1 or 2 is included as an electron transport auxiliary layer material, efficiency of the organic EL device may be increased due to a triplet-triplet fusion (TTF) effect.
  • TTF triplet-triplet fusion
  • the compound of Chemical Formula 1 or 2 may prevent excitons generated in the light-emitting layer from diffusing into the electron transport layer adjacent to the light-emitting layer. Accordingly, the number of excitons contributing to light emission in the light-emitting layer may be increased to improve luminous efficiency of the device, and durability and stability of the device may be improved to effectively increase the lifespan of the device.
  • the structure of the organic EL device of the present invention described above is not particularly limited, and may include, for example, an anode 100, one or more organic layers 300 and a cathode 200 sequentially stacked on a substrate (see FIGS. 1 to 3 ).
  • it may have a structure in which an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic layer.
  • the organic EL device may have a structure including, on a substrate, an anode 100, a hole injection layer 310, a hole transport layer 320, a light-emitting layer 330, an electron transport layer 340 and a cathode 200 sequentially stacked.
  • an electron injection layer 350 may be positioned between the electron transport layer 340 and the cathode 200.
  • an electron transport auxiliary layer 360 may be positioned between the light-emitting layer 330 and the electron transport layer 340 (see FIG. 3 ).
  • the organic EL device of the present invention may be manufactured by forming an organic layer and an electrode with materials and methods known in the art, except that at least one of the organic layer 300 (e.g., the electron transport layer 340, the electron transport auxiliary layer 360) includes the compound represented by Chemical Formula 1 or 2.
  • the organic layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer method.
  • the substrate applicable in the present invention is not particularly limited, and non-limiting examples thereof may include a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, and a sheet.
  • examples of the anode material may include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold or an alloy thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); combination of oxide with metal such as ZnO:Al or SnO 2 :Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly [3,4-(ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; and carbon black or the like.
  • metals such as vanadium, chromium, copper, zinc, and gold or an alloy thereof
  • metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); combination of oxide with metal such as ZnO:Al or SnO 2 :Sb
  • conductive polymers such as polythiophene, poly(3-
  • cathode material may include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; a multi-layered material such as LiF/Al or LiO 2 /Al or the like.
  • Compound 201 (2.4 g, yield: 55 %) was prepared in the same manner as in Synthesis Example 14, except that 2-(9,9-diphenyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan was used instead of 2-(9,9-dimethyl-9H-fluoren-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan used in Synthesis Example 14.
  • Compound 206 (2.3 g, yield: 52 %) was prepared in the same manner as in Synthesis Example 15, except that 2-(9,9'-spirobi[fluoren]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan was used instead of 2-(9,9-dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan used in Synthesis Example 15.
  • a glass substrate thin-film-coated with indium tin oxide (ITO) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing with distilled water was completed, the glass substrate was ultrasonically cleaned with a solvent, such as isopropyl alcohol, acetone and methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech) cleaned for 5 minutes using UV, and then transferred to a vacuum evaporator.
  • a solvent such as isopropyl alcohol, acetone and methanol
  • Blue organic EL devices of Embodiments 2 to 11 were prepared in the same manner as in Embodiment 1, except that Compounds shown in Table 1 were respectively used instead of Compound 3 which was used as an electron transport layer material in the forming of the electron transport layer in Embodiment 1.
  • a blue organic EL device was prepared in the same manner as in Embodiment 1, except that Alq 3 was used instead of Compound 3 which was used as an electron transport layer material in Embodiment 1.
  • a structure of Alq 3 used in such a case was as follows.
  • a blue organic EL device was prepared in the same manner as in Embodiment 1, except that Compound 3 which was used as an electron transport layer material in Embodiment 1 was not used.
  • a blue organic EL device was prepared in the same manner as in Embodiment 1, except that T-1 was used instead of Compound 3 which was used as an electron transport layer material in Embodiment 1.
  • a structure of T-1 used in such a case was as follows.
  • a blue organic EL device was prepared in the same manner as in Embodiment 1, except that T-2 was used instead of Compound 3 which was used as an electron transport layer material in Embodiment 1.
  • a structure of T-2 used in such a case was as follows.
  • the blue organic EL devices of Embodiments 1 to 11 in which the compounds of the present invention were used in the electron transport layer exhibited excellent performance in terms of the driving voltage, the emission peak and the current efficiency, as compared to the blue organic EL device in Comparative Example 1 in which conventional Alq 3 was used in the electron transport layer and the blue organic EL device in Comparative Example 2 in which the electron transport layer was not included.
  • a glass substrate thin-film-coated with indium tin oxide (ITO) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing with distilled water was completed, the glass substrate was ultrasonically cleaned with a solvent, such as isopropyl alcohol, acetone and methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech) cleaned for 5 minutes using UV, and then transferred to a vacuum evaporator.
  • a solvent such as isopropyl alcohol, acetone and methanol
  • Embodiments 13 to 22 were prepared in the same manner as in Embodiment 12, except that Compounds shown in Table 2 were respectively used instead of Compound 12 which was used as an electron transport auxiliary layer material in Embodiment 12.
  • a blue organic EL device was prepared in the same manner as in Embodiment 12, except that Compound 12 which was used as an electron transport auxiliary layer material in Embodiment 12 was not used and that Alq 3 , an electron transport layer material, was deposited to 30 nm instead of 25 nm.
  • a blue organic EL device was prepared in the same manner as in Embodiment 12, except that T-1 was used instead of Compound 12 which was used as an electron transport auxiliary layer material in Embodiment 12.
  • the structure of T-1 used in such a case is the same as that described in Comparative Example 3, and thus it will be omitted.
  • a blue organic EL device was prepared in the same manner as in Embodiment 12, except that T-2 was used instead of Compound 12 which was used as an electron transport auxiliary layer material in Embodiment 12.
  • the structure of T-2 used in such a case is the same as that described in Comparative Example 4, and thus it will be omitted.

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EP20890077.9A 2019-11-21 2020-11-19 Organische verbindung und organische elektrolumineszente vorrichtung mit verwendung davon Pending EP4063353A4 (de)

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KR102611317B1 (ko) * 2014-12-24 2023-12-07 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR102394374B1 (ko) * 2016-01-18 2022-05-04 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자
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